Jump to main content
Jump to site search

Issue 38, 2016
Previous Article Next Article

Synthesis of quinolines and naphthyridines via catalytic retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes or nicotinaldehydes

Author affiliations

Abstract

A Cu(I)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα–Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.

Graphical abstract: Synthesis of quinolines and naphthyridines via catalytic retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes or nicotinaldehydes

Back to tab navigation

Supplementary files

Publication details

The article was received on 07 Jul 2016, accepted on 25 Aug 2016 and first published on 25 Aug 2016


Article type: Paper
DOI: 10.1039/C6OB01452F
Citation: Org. Biomol. Chem., 2016,14, 8966-8970
  •   Request permissions

    Synthesis of quinolines and naphthyridines via catalytic retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes or nicotinaldehydes

    S. Zhang and Z. Deng, Org. Biomol. Chem., 2016, 14, 8966
    DOI: 10.1039/C6OB01452F

Search articles by author

Spotlight

Advertisements